Impact of structural differences in carcinopreventive agents indole-3-carbinol and 3,3′-diindolylmethane on biological activity. An X-ray, 1H–14N NQDR, 13C CP/MAS NMR, and periodic hybrid DFT study

European Journal of Pharmaceutical Sciences - Tập 77 - Trang 141-153 - 2015
Jolanta Natalia Latosińska1, Magdalena Latosińska1, Marek Szafrański1, Janez Seliger2,3, Veselko Žagar3, Dorota V. Burchardt4
1Faculty of Physics, Adam Mickiewicz University, Umultowska 85, 61-614 Poznań, Poland
2Faculty of Mathematics and Physics, University of Ljubljana, Jadranska 19, 1000 Ljubljana, Slovenia
3Jozef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia
4Department of Paediatric Dentistry, Poznan University of Medical Sciences, Bukowska 70, 60-812 Poznań, Poland

Tài liệu tham khảo

Aggarwal, 2005, Molecular targets and anticancer potential of indole-3-carbinol and its derivatives, Cell cycle (Georgetown, Tex.), 4, 1201, 10.4161/cc.4.9.1993 Ahmad, 2010, Anticancer properties of indole compounds: mechanism of apoptosis induction and role in chemotherapy, Curr. Drug Targets, 11, 652, 10.2174/138945010791170923 Allen, 2002, The Cambridge Structural Database: a quarter of a million crystal structures and rising, Acta Cryst. B, 58, 380, 10.1107/S0108768102003890 Anderton, 2004, Physiological modeling of formulated and crystalline 3,3′-diindolylmethane pharmacokinetics following oral administration in mice, Drug Metab. Dispos., 32, 632, 10.1124/dmd.32.6.632 Antonio, 2014, Phytotherapy in primary health care, Rev. Saude Publica, 48, 541, 10.1590/S0102-311X2007000600021 Arnao, 1996, Indole-3-carbinol as a scavenger of free radicals, Biochem. Mol. Biol. Int., 39, 1125 Aronchik, 2014, The anti-proliferative response of indole-3-carbinol in human melanoma cells is triggered by an interaction with NEDD4-1 and disruption of wild-type PTEN degradation, Mol. Cancer Res., 12, 1621, 10.1158/1541-7786.MCR-14-0018 Auborn, 2003, Lifespan is prolonged in autoimmune-prone (NZB/NZW) F1 mice fed a diet supplemented with indole-3-carbinol, J. Nutr., 133, 3610, 10.1093/jn/133.11.3610 Bailey, 1987, Enhancement of carcinogenesis by the natural anticarcinogen indole-3-carbinol, J. Natl Cancer Inst., 78, 931 Becke, 1993, A new mixing of Hartree–Fock and local density-functional theories, J. Chem. Phys., 98, 1372, 10.1063/1.464304 Bell, 2000, Placebo-controlled trial of indole-3-carbinol in the treatment of CIN, Gynecol. Oncol., 78, 123, 10.1006/gyno.2000.5847 Blinc, 1972, 14N NQR spectroscopy of some amino acids and nucleic bases via double resonance in the laboratory frame, J. Chem. Phys., 57, 5087, 10.1063/1.1678193 Bonnesen, 2001, Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines, Cancer Res., 61, 6120 Bradlow, 2008, Review. Indole-3-carbinol as a chemoprotective agent in breast and prostate cancer, In vivo (Athens, Greece), 22, 441 Bradlow, 1999, Multifunctional aspects of the action of indole-3-carbinol as an antitumor agent, Ann. N. Y. Acad. Sci., 889, 204, 10.1111/j.1749-6632.1999.tb08736.x Brandi, 2003, A new indole-3-carbinol tetrameric derivative inhibits cyclin-dependent kinase 6 expression, and induces G1 cell cycle arrest in both estrogen-dependent and estrogen-independent breast cancer cell lines, Cancer Res., 63, 4028 Burton, 1986, 13C NMR spectra of substituted indoles, Magn. Reson. Chem., 24, 829, 10.1002/mrc.1260240919 Chinni, 2001, Indole-3-carbinol (I3C) induced cell growth inhibition, G1 cell cycle arrest and apoptosis in prostate cancer cells, Oncogene, 20, 2927, 10.1038/sj.onc.1204365 Clark, 2005, CASTEP reference, Z. Krist., 220, 567 Cover, 1998, Indole-3-carbinol inhibits the expression of cyclin-dependent kinase-6 and induces a G1 cell cycle arrest of human breast cancer cells independent of estrogen receptor signaling, J. Bol. Chem., 273, 3838, 10.1074/jbc.273.7.3838 Delley, 1990, An all-electron numerical method for solving the local density functional for polyatomic molecules, J. Chem. Phys., 92, 508, 10.1063/1.458452 Delley, 2000, From molecules to solids with the DMol3 approach, J. Chem. Phys., 113, 7756, 10.1063/1.1316015 Ferlay, 2010, Estimates of worldwide burden of cancer in 2008: GLOBOCAN 2008, Int. J. Cancer, 127, 2893, 10.1002/ijc.25516 Fowke, 2007, Head and neck cancer: a case for inhibition by isothiocyanates and indoles from cruciferous vegetables, Eur. J. Cancer Prev., 16, 348, 10.1097/01.cej.0000236258.80522.fb Frisch, 2009 Grimme, 2006, Semiempirical GGA-type density functional constructed with a long-range dispersion correction, J. Comput. Chem., 27, 1787, 10.1002/jcc.20495 Hammer, 1999, Improved adsorption energetics within density-functional theory using revised Perdew–Burke–Ernzerhof functionals, Phys. Rev. B, 59, 7413, 10.1103/PhysRevB.59.7413 Hecht, 2000, Inhibition of carcinogenesis by isothiocyanates, Drug Metab. Rev., 32, 395, 10.1081/DMR-100102342 Hexem, 1981, Influence of nitrogen-14 on carbon-13 NMR spectra of solids, J. Am. Chem. Soc., 103, 224, 10.1021/ja00391a057 Higdon, 2007, Cruciferous vegetables and human cancer risk: epidemiologic evidence and mechanistic basis, Pharmacol. Res., 55, 224, 10.1016/j.phrs.2007.01.009 Hsu, 2006, Indole-3-carbinol mediated cell cycle arrest of LNCaP human prostate cancer cells requires the induced production of activated p53 tumor suppressor protein, Biochem. Pharmacol., 72, 1714, 10.1016/j.bcp.2006.08.012 Jin, 1999, Indole-3-carbinol prevents cervical cancer in human papilloma virus type 16 (HPV16) transgenic mice, Cancer Res., 59, 3991 Kelloff, 2000, Perspectives on cancer chemoprevention research and drug development, Adv. Cancer Res., 78, 199, 10.1016/S0065-230X(08)61026-X Kohn, 1965, Self-consistent equations including exchange and correlation effects, Phys. Rev., 140, A1133, 10.1103/PhysRev.140.A1133 Kristal, 2002, Brassica vegetables and prostate cancer risk: a review of the epidemiological evidence, Nutr. Cancer, 42, 1, 10.1207/S15327914NC421_1 Kwon, 2007, Cancer chemoprevention by phytochemicals: potential molecular targets, biomarkers and animal models, Acta Pharmacol. Sin., 28, 1409, 10.1111/j.1745-7254.2007.00694.x Landis-Piwowar, 2014, Cancer chemoprevention: current state of the art, Cancer Growth Metastasis, 7, 19, 10.4137/CGM.S11288 Latosińska, 2003, NQR parameters: electric field gradient tensor and asymmetry parameter studied in terms of density functional theory, Int. J. Quant. Chem., 91, 284, 10.1002/qua.10451 Latosińska, 2005, Structure–activity study of thiazides by magnetic resonance methods (NQR, NMR, EPR) and DFT calculations, J. Mol. Graph. Model., 23, 329, 10.1016/j.jmgm.2004.11.001 Latosińska, 2007, Applications of nuclear quadrupole resonance spectroscopy in drug development, Expert Opin. Drug Discov., 2, 225, 10.1517/17460441.2.2.225 Latosińska, 2000, Analysis of the NQR parameters in 2-nitro-5-methylimidazole derivatives by quantum chemical calculations, Phys. Chem. Chem. Phys., 2, 145, 10.1039/a906295e Latosińska, 2013, Anticancer drug discovery—from serendipity to rational design, 35 Latosińska, 2014, Quantum-chemical insight into structure–reactivity relationship in 4,5,6,7-tetrahalogeno-1H-benzimidazoles: a combined X-ray, DSC, DFT/QTAIM, Hirshfeld surface-based, and molecular docking approach, J. Phys. Chem. A, 118, 2089, 10.1021/jp411547z Latosińska, 2014, Topology of the interactions pattern in pharmaceutically relevant polymorphs of methylxanthines (caffeine, theobromine, and theophylline): combined experimental (1H–14N nuclear quadrupole double resonance) and computational (DFT and Hirshfeld-based) study, J. Chem. Inf. Model., 54, 2570, 10.1021/ci5004224 Latosińska, 2014, An insight into prototropism and supramolecular motifs in solid-state structures of allopurinol, hypoxanthine, xanthine, and uric acid. A 1H–14N NQDR spectroscopy, hybrid DFT/QTAIM, and Hirshfeld surface-based study, J. Phys. Chem. B, 118, 10837, 10.1021/jp504871y Lee, 2003, Beneficial and adverse effects of chemopreventive agents, Mutat. Res., 523–524, 265, 10.1016/S0027-5107(02)00342-1 Lee, 1988, Development of the Colle–Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B, 37, 785, 10.1103/PhysRevB.37.785 Levy, 1979, Universal variational functionals of electron densities, first-order density matrices, and natural spin-orbitals and solution of the v-representability problem, Proc. Natl. Acad. Sci. USA, 76, 6062, 10.1073/pnas.76.12.6062 Licznerska, 2013, Modulation of CYP19 expression by cabbage juices and their active components: indole-3-carbinol and 3,3′-diindolylmethene in human breast epithelial cell lines, Eur. J. Nutr., 52, 1483, 10.1007/s00394-012-0455-9 Machijima, 2009, Anti-adult T-cell leukemia/lymphoma effects of indole-3-carbinol, Retrovirology, 6, 7, 10.1186/1742-4690-6-7 Maciejewska, 2005, Structure in solid state of 3,3′-diindolylmethane derivatives, potent cytotoxic agents against human tumor cells, followed X-ray diffraction and 13C CP/MAS NMR analyses, J. Mol. Struct., 753, 53, 10.1016/j.molstruc.2005.05.035 Maciejewska, 2006, DNA-based electrochemical biosensors for monitoring of bis-indoles as potential antitumoral agents, chemistry, X-ray crystallography, Bioelectrochemistry, 69, 1, 10.1016/j.bioelechem.2005.09.003 Markushin, 2003, Spectral characterization of catechol estrogen quinone (CEQ)-derived DNA adducts and their identification in human breast tissue extract, Chem. Res. Toxicol., 16, 1107, 10.1021/tx0340854 Mehring, 1983 Monkhorst, 1976, Special points for Brillouin-zone integrations, Phys. Rev. B, 13, 5188, 10.1103/PhysRevB.13.5188 Morzyk-Ociepa, 2004, Structures and vibrational spectra of indole carboxylic acids. Part I. Indole-2-carboxylic acid, J. Mol. Struct., 688, 79, 10.1016/j.molstruc.2003.09.027 Murillo, 2001, Cruciferous vegetables and cancer prevention, Nutr. Cancer, 41, 17, 10.1080/01635581.2001.9680607 Perdew, 1996, Generalized gradient approximation made simple, Phys. Rev. Lett., 77, 3865, 10.1103/PhysRevLett.77.3865 Perdew, 2008, Restoring the density-gradient expansion for exchange in solids and surfaces, Phys. Rev. Lett., 100, 136406, 10.1103/PhysRevLett.100.136406 Pickard, 2001, All-electron magnetic response with pseudopotentials: NMR chemical shifts, Phys. Rev. B, 63, 245101, 10.1103/PhysRevB.63.245101 Politzer, 2001, Molecular surface electrostatic potentials in relation to noncovalent interactions in biological systems, Int. J. Quantum Chem., 85, 676, 10.1002/qua.1706 Poornima, 2014, Regulation of carbohydrate metabolism by indole-3-carbinol and its metabolite 3,3′-diindolylmethane in high-fat diet-induced C57BL/6J mice, Mol. Cell. Biochem., 385, 7, 10.1007/s11010-013-1808-2 Pyykkö, 2008, Year-2008 nuclear quadrupole moments, Mol. Phys., 106, 1965, 10.1080/00268970802018367 Raj, 2008, Synergistic action of dietary phyto-antioxidants on survival and proliferation of ovarian cancer cells, Gynecol. Oncol., 110, 432, 10.1016/j.ygyno.2008.05.001 Reed, 2005, A phase I study of indole-3-carbinol in women: tolerability and effects, Cancer Epidemiol. Biomarkers Prev., 14, 1953, 10.1158/1055-9965.EPI-05-0121 Roychowdhury, 1975, The crystal structure of indole, Acta Cryst. B, 31, 1559, 10.1107/S0567740875005687 Sarkar, 2004, Indole-3-carbinol and prostate cancer, J. Nutr., 134, 3493, 10.1093/jn/134.12.3493S Seliger, 2008, Measurement of the 14N nuclear quadrupole resonance frequencies by the solid effect, J. Magn. Reson., 193, 54, 10.1016/j.jmr.2008.04.020 Seliger, 2008, Sensitivity of nuclear-quadrupole double-resonance detection of half-integer spin nuclei, J. Magn. Reson., 194, 175, 10.1016/j.jmr.2008.06.021 Seliger, 2012, New methods for detection of 14N NQR frequencies, Appl. Magn. Reson., 43, 469, 10.1007/s00723-011-0303-8 Seliger, 1976, Proton-14N double resonance study of the structural phase transitions in the perovskite type layer compound (CH3NH3)2CdCl4, Z. Phys. B, 25, 189, 10.1007/BF01320180 Seliger, 1994, 1H–14N nuclear quadrupole double resonance with multiple frequency sweeps, Z. Naturforsch., 49, 1 Seliger, 1994, A new highly sensitive 1H–14N nuclear-quadrupole double-resonance technique, J. Magn. Reson. A, 106, 214, 10.1006/jmra.1994.1027 Sheldrick, 2008, A short history of SHELX, Acta Cryst. A, 64, 112, 10.1107/S0108767307043930 Singh, 2006, Mechanisms of action of novel agents for prostate cancer chemoprevention, Endocr. Relat. Cancer, 13, 751, 10.1677/erc.1.01126 Smith, 2003, Indole-3-carboxylic acid, Acta Cryst. E, 59, o1766, 10.1107/S1600536803022670 Spackman, 2009, Hirshfeld surface analysis, CrystEngComm, 11, 19, 10.1039/B818330A Spackman, 2002, Fingerprinting intermolecular interactions in molecular crystals, CrystEngComm, 4, 378, 10.1039/B203191B Tkatchenko, 2009, Accurate molecular van der Waals interactions from ground-state electron density and free-atom reference data, Phys. Rev. Lett., 102, 073005, 10.1103/PhysRevLett.102.073005 Weng, 2008, Indole-3-carbinol as a chemopreventive and anti-cancer agent, Cancer Lett., 262, 153, 10.1016/j.canlet.2008.01.033 Wishart, 2007, HMDB: the human metabolome database, Nucleic Acids Res., 35, D521, 10.1093/nar/gkl923 Wong, 1997, Dose-ranging study of indole-3-carbinol for breast cancer prevention, J. Cell. Biochem., 28–29, 111, 10.1002/(SICI)1097-4644(1997)28/29+<111::AID-JCB12>3.0.CO;2-K Wu, 2006, More accurate generalized gradient approximation for solids, Phys. Rev. B, 73, 235116, 10.1103/PhysRevB.73.235116 X1, 2010. X1. Oxford Diffraction CrysAlisPro: Data Collection and Processing Software for X-Ray Diffractometers GUI, Version 4. Agilent Technologies, Santa Clara, CA. Yan, 2009, Indole-3-carbinol improves survival in lupus-prone mice by inducing tandem B- and T-cell differentiation blockades, Clin. Immunol., 131, 481, 10.1016/j.clim.2009.01.013 Zhang, 2003, Indole-3-carbinol induces a G1 cell cycle arrest and inhibits prostate-specific antigen production in human LNCaP prostate carcinoma cells, Cancer, 98, 2511, 10.1002/cncr.11844